Method of treating hair with hydroxyether amides of polyacrylic acids



United States Patent Ofilice 3,016,333 Patented Jan. 9, 1262 This invention relates to the. improvement in hair dressing compositions. More particularly, the invention relates to the embodiment into hair dressing preparations of the reaction product of an acrylamide polymer and an alkylene oxide. According to the invention, I have discovered that the incorporation of a polymeric reaction product of (A) an acrylamide polymer, as hereinafter more specifically defined, and (B) an alkylene oxide into various hair dressing, shampooing, or grooming preparations produces an unexpected and highly desirable appearance and texture to the hair. The effect on the hair of a reaction product of this type provides a marked contrast to the effect obtained by various available compositions on the market containing an assortment of ingredients. The most pronounced advantages of hair preparations of the invention containing this agent, i.e. the alkylene oxide-acrylamide type polymer reaction product, are the complete absence of the dry or brittle stage of the hair upon drying, and the freedom from flaking. Following a treatment with a composition containing this agent, the hair remains soft and pliable without being sticky or pasty. Due to the retention of a thin uniform film of the polymeric agent on the individual hairfilaments,

the hair has improved texture and retains a significant moisture content which maintains the initial well groomed effect on the hair to give it a long-lasting, just-combed appearance.

An object of the present invention is to provide a novel improved water-soluble and alcohol-soluble polymeric agent for hair grooming preparations. Another object is the provision in either a dry or liquid form, a readily soluble polymeric reaction product for hair grooming preparations which provides a non-sticky, non-pasty hygroscopic film on the hair filaments. Other objects and advantages will become apparent as the description of the invention proceeds.

In preparing the polymeric agent for use according to the invention, the following illustrative procedure, in which polyacrylamide is representative of the acrylamide type polymeric reactant and ethylene oxide is representative of the alkylene oxide, may be employed. The reaction is carried out by dissolving polyacrylamide in a solvent, preferably water, containing a hydroxide or alcoholate of an alkali metal such as sodium hydroxide and charged with ethylene oxide and thereafter reacting the mixture under heat and pressure. The reaction may also be conducted at elevated temperatures and at atmospheric pressure providing an extended reaction period is employed.

The amount of alkylene oxide may vary over a fairly wide range and depends on the properties desired, al though it is found that preferred properties for the objects of the present invention are derived when the mole ratio of alkylene oxide to polymer is between 2.0 and 25.0 and preferably between 5.0 and 20. In addition to ethylene oxide, other alkylene oxides such as propylene oxide, n-butylene oxide, isobutylene oxide and the like may also be employed.

R1 o H2C=i J-N-R R3 wherein R is hydrogen, a methyl or an ethyl group; R is hydrogen or an alkyl hydroxy radical of not more than 5 carbon atoms and R is hydrogen, an alkyl radical of 1-4 carbon atoms, or an alkyl hydroxy radical of not more than 5 carbon atoms. In addition to acrylamide, suitable monomers of this formula are methacrylamide, N-methyl-acrylamide, N-tertiary butyl acrylamide,'N-hydroxyethyl acrylamide, N-methylol acrylamide and the like.

In addition to homopolymers of the above acrylamide type compounds, copolym'ers thereof with minor amounts not exceeding 20% and preferably not exceeding 15% of the total polymer of polymerizable compounds, such as acrylonitrile, vinyl aromatic monomers, e.g., styrene or methylstyrene, dimethylstyrene, acrylic and methacrylic acids and salts thereof, ethyl and methyl acrylate and methacrylate, and the like may be employed as the polymer component in the reaction with the alkylene oxide.

In addition to sodium hydroxide, other alkali metal hydroxides, alcoholates or carbonates such as potassium or lithium hydroxide, sodium ethylate, potassium ethylate, sodium -or potassium carbonate and the like may be used as catalyst. Organic bases, e.g., triethylamine, triethanolamine, trimethyl benzyl ammonium hydroxide, available as Triton B, pyridine and the likernay also be usefully employed.

The following example is illustrative of the procedure by which the polymeric agent may be prepared.

An autoclave is charged with a solution containing 4.0 parts polyacrylamide, 0.06 part of sodium hydroxide, and 95.04 parts of water. To this solution is charged 44 parts of ethylene oxide and the mixtureheated to 100 C. under pressure. After reaction is complete as indicated by a drop in the exotherm, the water is evaporated. The remaining syrup may then be dissolved in alcohol or water to the desired concentration. As an alternate procedure using like amounts of reactants, the ethylene oxide may be bubbled through the mixture at atmospheric pressure and at a temperature of about to C. for a period of several hours.

The polymeric agent herein described may be readily incorporated, without special formulating steps, into various'hair treating formulations, the procedures for the preparation thereof which are known to those skilled in the art. Included within the contemplation of my invention as uses for the polymeric agent are various hair formulations, such as shampoos, creams, sprays, lacquers, rinses, lotions and the like. In the case of liquid preparations such as rinses, sprays or shampoos, amounts below about 10% and preferably between 0.5 and 3% of the polymeric agent is generally sufficient, whereas in cream preparations which are applied to the hair more sparingly a higher concentration, i.e., up to about 20%, may be used, although amounts not ex ceeding about 15% are generally preferred.

The polymeric agents incorporated into the hair formulations according to the invention are non-toxic, odorless and Substantially chemically inert compositions. These agents have good stability so that they may be stored Without separation from the hair treating formulation and without causing decomposition or failure of the efficiency of the preparation. storage, no loss of homogeneity or separation of components from such hair preparations due to these polymeric ingredients has been found. The inclusion of the polymeric agent in hair formulations as herein described in no way precludes the concurrent use of various known Even after prolonged hair conditioning components such as the various organic and inorganic salts, colorants, plasticizers, oils, greases, e.g., lanolin, or medications.

The invention is further illustrated by the following examples. All parts stated are parts by weight unless otherwise specified.

Example 1 The following formulation is incorporated into an aerosol spray:

Percent Polyacrylamide-ethylene oxide resin 3.0 Perfume 0.2 Lanolin derivative 0.3 Anhydrous ethanol 21.5 Propellant, Freon 11, CCl F 75.0

The ingredients are applied as a spray and give the desirable properties mentioned in Example 1. A particu larly durable permanent set of the hair arrangement is obtained when a further spraying of the arranged hair is made with the formulation.

Example 3 An aqueous concentrate of about polyacrylamideethylene oxide reaction product is prepared which can be readily diluted for use. One part of the concentrate is diluted with to 20 parts of Water. The resulting solution is a useful hair dressing agent. When combed into the hair, a long-lasting neat appearance is imparted thereto without presentingthe greasy appearance to the hair which is produced by many available compositions.

Example 4 One part of the concentrate described in Example 3 is diluted with 10 to 20 parts of water, 0.1 part of the water-soluble color aniline blue, 0.15 part of a brightener, Calcofluor White RW, and 2 parts of a 5% alcohol solution of lgeraniol as a perfumant is added and the solution sprayed onto the hair after the hair has been set. On drying, a thin, slightly hydroscopic, clear film is left on the hair strands which holds them in place and otherwise makes them easily manageable. No flakiness whatever is observed upon drying of the hair.

Example 5 A shampoo formulation consisting of 68.9 parts water, 0.1 part brightener, 10 parts ethanol, 20 parts detergent and 1 part polyacrylamide-ethylene oxide reaction product is used for shampooing the hair. The polymeric agent imparts stability to the foam and leaves a thin, slightly ihydroscopic, clear film on the hair strands that renders them more easily manageable.

No fiakiness is found when the hair is dried.

Example 6 treated hair curled and retained substantial gloss on drying, While the water-treated hair remained limp and substantially straight as when stretched. The latter, moreover, had noticeably less gloss.

Example 7 A preparation consisting of 0.5 part polyacrylamideethylene oxide reaction product, 100 parts water, watersoluble color and perfume is applied to hair, and the treated hair is then divided into tresses, wound on bars, and allowed to dry. The polyacrylamide-ethylene oxide treated hair remains in place for at least 10 times longer (the observed period) than a control treated with a composition lacking the polyacrylamide-ethylene oxide agent. The hair treated with the formulation containing the polymeric agent is easier to manage and has a more attractive sheen than untreated hair, even after considerable rushing of the untreated hair. The thin, transparent film formed on the polyacrylamide-ethylene oxide treated hair is not easily removed when merely wetted with water, but may be removed with shampoo.

What is claimed is:

1. A method of treating hair which comprises applying to said hair a composition comprising an alcoholic solution containing up to 20% by weight of a water soluble and an alcohol soluble reaction product of (A) a polymer of an acrylamido compound having the formula:

RI 0 IEI2(}=(II(HJNR2 wherein R isa member selected from the group consisting of hydrogen, methyl and ethyl; R is a member selected from the group consisting of hydrogen and an alkyl hydroxy radical of not more than 5 carbon atoms and R is a member of the group consisting of hydrogen, an alkyl radical having from 1 to 4 carbon atoms and an alkyl hydroxy radical of not more than 5 carbon atoms, and (B) an alkylene oxide wherein the mol ratio of said alkylene oxide to polymer is between 5:1 and 20:1 respectively.

2. A method of treating hair which comprises applying to said hair a composition comprising an alcoholic solution containing up to 20% by weight of a water soluble and an alcohol soluble reaction product of (A) a polymer of an acrylamido compound having the formula:

wherein R is a member selected from the group consisting of hydrogen, methyl and ethyl; R is a member selected from the group consisting of hydrogen and an alkyl hydroxy radical of not more than 5 carbon atoms and R is a member of the group consisting of hydrogen, an alkyl radical having from 1 to 4 carbon atoms and an alkyl hydroxy radical of not more than 5 carbon atoms, and (B) ethylene oxide wherein the mol ratio of said ethylene oxide to polymer is between 5:1 and 20:1 respectively.

References Cited in the file of this patent UNITED STATES PATENTS 2,305,356 Luckenbach Dec. 15, 1942 2,803,607 Stroh et a1. Aug. 20, 1957 2,808,397 Stroh et a1. Oct. 1, 1957 2,842,462 Haas et al July 8, 1958 OTHER REFERENCES Mills et al.: 15. Cosmetic Chemists, vol. 7, No. 5, September 1956, pp. 466-475. 

1. A METHOD OF TREATING HAIR WHICH COMPRISES APPLYING TO SAID HAIR A COMPOSITION COMPRISING AN ALCOHOLIC SOLUTION CONTAINING UP TO 20% BY WEIGHT OF A WATER SOLUBLE AND AN ALCOHOL SOLUBLE REACTION PRODUCT OF (A) A POLYMER OF AN ACRYLAMIDO COMPOUND HAVING THE FORMULA: 